Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols

Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-12, Vol.134 (49), p.19965-19968
Main Authors: Luan, Yi, Schaus, Scott E
Format: Article
Language:English
Subjects:
Benzoquinones - chemical synthesis
Benzoquinones - chemistry
Boronic Acids - chemistry
Catalysis
Indolequinones - chemistry
Molecular Structure
Phenols - chemical synthesis
Phenols - chemistry
Stereoisomerism
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Summary:Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja309076g